2-heterosubstituted 3-aryl-4H-1-benzopyran-4-ones as novel therapeutics in breast cancer
View Patent ↗The present invention provides 2-heterosubstituted 3-aryl-4H-benzopyran-4-one compounds for the treatment of cancers, namely breast cancer. This invention further provides a method of synthesis of 2-(alkylthio)isoflavones that can be carried out at ambient conditions. This invention further provides a method of synthesis of the 2-heterosubstituted 3-aryl-4H-benzopyran-4-one from a 2-(alkylthio)isoflavone. The invention further provides methods of using the 2-heterosubstituted 3-aryl-4H-benzopyran-4-one compounds for the treatment of breast cancer in mammals.
1. A compound of formula A:
wherein
X is selected from the group consisting of O, N, S, SO, and SO 2 ;
R 1 and R 2 can be the same or different and are selected from the group consisting of H, OH, OCH 3 , OCH 2 CH 3 , OCH 2 C 6 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CN, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , NO 2 , F, Cl, Br, CF 3 , SH, SCH 3 , SCH 2 CH 3 , OCOCH 3 , OCOC(CH 3 ) 3 , and OCOCH 2 COOH;
R 3 is
2. The compound of claim 1 , wherein
X is selected from S and O;
R 1 is selected from OH, OCH 3 , and OC 6 H 5 ; and
R 2 is selected from H, OH, CH 3 , and OCH 3 .
3. The compound of claim 2 , wherein X is S, R 1 is OC 6 H 5 , and R 2 is OCH 3 .
4. The compound of claim 2 , wherein X is S, R 1 is OH, and R 2 is OH.
5. A method for treating, inhibiting, or delaying the onset of a breast cancer in a subject in need of such treatment; the method comprising administering a therapeutically effective amount of compound A:
wherein
X is selected from the group consisting of O, N, S, SO, and SO 2 ;
R 1 and R 2 can be the same or different and are selected from the group consisting of H, OH, OCH 3 , OCH 2 CH 3 , OCH 2 C 6 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CN, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , NO 2 , F, Cl, Br, CF 3 , SH, SCH 3 , SCH 2 CH 3 , OCOCH 3 , OCOC(CH 3 ) 3 , and OCOCH 2 COOH;
R 3 is
to the subject in need of such treatment.
6. The method of claim 5 wherein the cancer is hormone-dependent breast cancer.